CN104237475B - A kind of method of the ester content of 1,3 2 oleic acid of indirect determination, 2 palmitic acid three - Google Patents
A kind of method of the ester content of 1,3 2 oleic acid of indirect determination, 2 palmitic acid three Download PDFInfo
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Abstract
The present invention relates to chemical analysis technology field, more particularly to a kind of indirect measurement method of the ester content of 2 palmitic acid of 1,3 two oleic acid three.This method directly determines the active part of the ester (OPO) of 1,3 two oleic acid, 2 palmitic acid three, so as to which active OPO content further be calculated.This method directly reflects OPO effective performance, so its content has directly corresponded to validity of the OPO as food additives.OPO forms after methods described indirect determination digestion, it is very easy to distinguish 2 P of sn, for non-2 P of sn isomer, can easily identifies, avoid faking.
Description
Technical field
It is sweet more particularly to a kind of oleic acid -2- palmitic acids of 1,3- in dairy products bis- the present invention relates to chemical analysis technology field
The indirect determination method of oily three ester contents.
Background technology
With expanding economy, growth in the living standard, for the consumption figure more and more higher of infant food.Baby children
Youngster's body is small, and physiological function is not yet ripe, but is normally grown to reach, and the heat demand of per kilogram of body weight is into
More than two times of people, if mainly with energy needed for carbohydrate and protein provision, every gram of heat that can only supply 16KJ, so
Amount must be quite big, and it is a no small burden for very perfect baby that digestive function, which is not also,；And grease can be with
The heat of more than two times of supply protein or carbohydrate is every gram of 38KJ heat, thus it is fatty must be indispensable in infant food
Material.
OPO (OPO) is a kind of new resource food that the Ministry of Public Health in 2008 newly increases,
It is analogous to a kind of triglycerides of human milk fat.About 70% palmitic acid is attached at the sn-2 of triglycerides in human milk fat
On position, and sn-1,3 are mainly unrighted acid.Palmitic acid is the important production capacity aliphatic acid of human body, and it is on triglycerides
Position it is digested and absorption has a great impact, the palmitic acid on sn-2 positions can be inhaled in the form of the monoglyceride of sn-2 positions
Receive, and sn-1, the palmitic acid on 3 then easily forms insoluble salt with mineral matter (calcium, magnesium etc.) and is lost, while also results in ore deposit
The loss of matter and energy.
Digestion process of the OPO triglycerides in baby intestinal can be briefly described as following steps：
A) fatty restriction endonuclease will be located at the aliphatic acid excision of triglycerides 1,3, form 2-monoglyceride.
B) undersaturated free oleic acid is solvable, and is efficiently absorbed.
C) 2- positions palmitic acid monoglyceride is efficiently absorbed.
And in cow's milk and most of baby formula milk powders on the market (addition common vegetable oil) fat knot
Structure exactly lacks OPO structural fatty structures, and its lipid structure is more to be existed with POP, PPO, PPP, OOP structure type, it means that
Up to 80% palmitic acid is connected on 1,3, and unsaturated fat pinolenic acid is connected on 2.These structures in digestion process,
The preferential palmitic acid discharged on 1,3, it can be combined with the mineral matter in enteron aisle, such as calcium phase, form calcium soap, be excluded body
Outside, so that baby loses substantial amounts of function palmitic acid and precious calcium.
Therefore, OPO has as a kind of new food additives and promotes body
To energy absorption, promote the bone minerals such as calcium, magnesium to absorb, alleviate the functions such as constipation of infantile.At present, the oleic acid -2- of 1,3- bis-
The research of the ester of palmitic acid three has progressively turned to industrialized production and application from laboratory stage abroad, and it is mainly used in
In dispensed food for baby.
Current many domestic and international researchers have all been carried out to research work fatty in infant food.1,3- bis- oleic acid-
The ester of 2- palmitic acids three (OPO) is a kind of breast milk structural fatty, will be largely used in dispensed food for baby.In
The magnificent Ministry of Public Health of people's republic bulletin (2010 No. 1) regulation requires that OPO is applicable model
Enclosing for dispensed food for baby, larger infants and young's formula food, preschool child's formula food, its amount of reinforcement is 24~
96g/kg, its amount is in terms of OPO sterling.
Palmitic acid is the most important aliphatic acid of infant physical growth, is provided for the growing of body, brain activity, metabolism
Energy, palmitic acid are easiest to be digested by infant when being incorporated in the Sn-2 positions of triglycerides, can promote body to energy matter
The absorption of (fat), and in Sn-1,3 then can not largely be absorbed, because Sn-1, the palmitic acid of 3 is in pancreas fat
Free palmitic acid is formed under enzyme effect, and palmitic acid fusing point (63 DEG C) is higher than body temperature, holds under the sour environment of small intestine
Saponification easily occurs with mineral matter, forms insoluble salt, is finally excreted, but the palmitic acid on Sn-2 positions then can
It is absorbed by the body in the form of Sn-2 palmitic acid monoglycerides.Sn-2 positions palmitic acid can also promote the bone minerals such as calcium, magnesium
Absorption, promote the growth of infant's body bone, easily trigger rickets during calcium deficiency, human body remains nervimuscular emerging
Put forth energy, the participation for the calcium that the conduction of nerve impulse, the normal beats of heart are also required to.Current study show that Sn-2 positions palmitic acid is also right
Growing for infant has facilitation, it is not yet found that close adverse effect develop to baby development of Sn-2 position palmitic acids with
Research in terms of side effect.
Quantitative detection to OPO (OPO) has been studied, but more problems be present.
Existing detection method is mainly reflected in detection process, and detection object is OPO (OPO) sheet
Body, due to the presence of OPO isomers so that OOP and/or POO is inevitably mixed into detection process.These OOP,
POO can influence the accuracy of OPO testing result, disturb the judgement to validity of products energy.
The Ministry of Public Health defines two important parameters：
OPO contents ＞ 40%
Sn-2 positions palmitate ratio ＞ 52%
Highlight palmitic acid Sn-2 positions ratio.Breast milk composition, clinical data and international regulations only provide Sn-2 positions palm fibre
Palmitic acid acid ratio is as effective parameter of measurement.So OPO analysis method should answer two problems in product：That is the nutrition of baby
Need and new laws and regulations requirement.
Therefore, more accurate OPO (OPO) detection method is studied, there is notable meaning
Justice.
The content of the invention：
The present invention describes a kind of active portion by directly determining OPO (OPO)
Divide (active form), so as to which the method for OPO content further be calculated.
So-called OPO active parts refer to postdigestive OPO, that is, lose sn-1, the OPO of 3 oleic acid.
Meanwhile outside the O of sn-2 positions P, sn-1,3, in measure fat, other sn-1,3 P and sn-2 positions also be present
O。
Digestion process of the OPO triglycerides in baby intestinal includes following three parts：
1. the aliphatic acid that fatty restriction endonuclease will be located at triglycerides 1,3 is cut off, 2-monoglyceride is formed.
2. undersaturated free oleic acid is solvable, and is efficiently absorbed.
3.2-palmitic acid monoglyceride is efficiently absorbed.
Therefore, the OPO that baby digests form is detected, that is, loses sn-1, the OPO of 3 oleic acid, that is, OPO active portions
Divide, OPO effective performance is directly reflected, so its content has directly corresponded to validity of the OPO as food additives.
Existing direct detecting method, it is necessary to separate isomer OPO, OOP and POO, complex operation, resultant error
Greatly, it is difficult to effectively reflection OPO true efficiency.
Above-mentioned Indirect Detecting Method is such as used, OPO forms after measure digestion, then is very easy to distinguish sn-2 positions P and sn-2
Position O.This forms of OPO are only what baby really needed, for non-sn-2 positions P isomer, can easily identify, avoid making
It is false.
The method of the invention, the triglycerides in baby food can be separated, be handled by enzymolysis, digestion, then carried out
Detection sn-2 positions P and sn-1, the O of 3, then by can be calculated.
Methods described is used to determining OPO in dairy products, the dairy products include but is not limited to liquid milk, milk powder, formulated infant milk,
Yoghourt, sour cream, ice cream.
Citing：
How many OPO in mixture after digestion
1 OPO molecule may separate out：P and 2 sn-1, the O of 3 of 1 sn-2 position.That is, for OPO forms
Triglycerides, postdigestive sn-2 positions P and sn-1, the O of 3 should keep the relation of the amount of 1: 2 material.
If (sn-2 position P)/(sn-1,3 O) are less than or equal to 1: 2, illustrate in postdigestive result, exist outside OPO
Sn-1, the O of 3, then OPO content on the basis of sn-2 positions P content, should be calculated, i.e. the content of material of sn-2 positions P is exactly
OPO content of material.
If (sn-2 position P)/(sn-1, the O of 3) is more than 1: 2, illustrates in postdigestive result, exist outside OPO
Sn-2 positions P, then OPO content should be calculated, i.e., 1/2 (sn-1,3 O) material contains with sn-1, on the basis of the O of 3 content
Amount is exactly OPO content of material.
Simple example, if we, which detect, obtains the P of a sn-2 position, and four sn-1, the O of 3, then according to above-mentioned pass
System, we can determine whether an only OPO molecule.If we detect and obtain the P of three sn-2 positions, and four sn-1, the O of 3,
Then according to above-mentioned relation, two OPO molecules can be calculated in we.
In the method for the invention, the P (palmitic acid) of sn-2 positions, the O (oleic acid) of sn-2 positions content, using GB/
T24894-2010《The measure of the sweet three ester molecules 2- positions aliphatic acid composition of animal and plant fat》Detected.
Sn-1, the O (oleic acid) of 3 measure, by being calculated.Mono fatty acid is obtained by lipase hydrolysis, is used
GB/T22223-2008《Measure hydrolysis extraction-gas phase color of total fat, saturated fat (acid), unsaturated fat (acid) in food
Spectrometry》Total oleic acid content is detected, the sn-2 positions oleic acid content measured with reference to GB/T24894-2010, its difference is sn-1,3
O (oleic acid) content.
The OPO contents obtained by the above method, truly reflect OPO in dairy products
Content, so as to reflect formulated infant milk for the finger that effectively improves absorption of the baby for mineral matters such as energy and calcium and utilize
Mark.By using the inventive method, paying close attention to OPO contents, determining OPO active part, preferably complied with the natural battalion of baby
The demand of supporting, supports the healthy growth of baby.
The present invention uses Indirect Determination, both realizes analysis purpose, while meets nutritional requirement, is directly calculated
OPO contents, avoid the adulterated possibility of any active ingredient.
Embodiment：
Embodiment 1
The indirect detection OPO first steps：
Analysis dairy mixture obtains：
1. total fatty acids form
2.sn-2 positions aliphatic acid composition
Using GB/T24894-2010 as detection method, as a result for：
Total %P=3/9=33.3%；
The %P=1/3=33.3% of sn-2 positions
Total %O=6/9=66.7%
The %O=2/3=66.7% of sn-2 positions.
Embodiment 2
Indirect detection OPO second steps：
Calculated according to result：
1. sn-2 positions P content in total fat
2. sn-1+3 content in total fat
(1) sn-2 positions P accounts for the ratio of total fat：
Because the P of sn-2 positions accounts for 1/3 total fatty acids, sn-2 positions P accounts for the ratio of total fat：33.3%/3=
11.1%.
(2) sn-1+3 positions O accounts for the ratio of total fat：
Sn-2 positions O accounts for the ratio of total fat：66.7%/3=22.25%.
The %O of (total %O)-(%O of sn-2 positions)=sn-1+3 positions, so sn-1+3 positions O accounts for the ratio of total fat：
66.7%-22.25%=44.4%
Embodiment 3
The steps of indirect detection OPO the 3rd：
It is based on：
Sn-2 positions P accounts for total lipid content：11%
Sn-1+3 positions O accounts for total lipid content：44.4%
Calculate OPO：
According to sn-2 positions P
According to sn-1+3 positions O
We choose relative low value as limitation sex factor
The OPO calculated according to P：
The P content of every 1% sn-2 positions, 3% OPO contents are necessarily corresponded to,
I.e.：P content × 3=11.1% × 3=33.3% of sn-2 positions.
OPO is calculated according to O：
The O of every 1% sn-1+3 positions, 1.5% OPO contents are necessarily corresponded to,
I.e.：O content × 1.5=44.4%*1.5=66.7% of sn-1+3 positions.
The OPO contents calculated according to P are 33.3%
The OPO contents calculated according to O are 66.7%
Because 33.3% ＜ 66.6%, OPO contents are 33.3%, i.e., are disappeared using indirect Determination in the form of OPO
The material of change, as a result correctly.
Embodiment 4
The present embodiment is by the comparative determinations of OPO contents, to illustrate that the inventive method contains to effective OPO in formulated infant milk
The characteristics of measure of amount.Sample 1,2,3 comes from InFatTM, be AAK and Enzymotec leading grease company of co-partnership company
The product of (Advanced Lipids), it is a kind of lipid ingredient rich in beta- palmitates.
Palm oil (palm oil) and breast milk have similar aliphatic acid composition, are commercially available prod, to contrast.
Measure：
Above-mentioned detection uses GB/T22223-2008《Total fat in food, saturated fat (acid), unsaturated fat (acid)
Measure hydrolysis extraction-gas chromatography》、GB/T24894-2010《The sweet three ester molecules 2- positions aliphatic acid composition of animal and plant fat
Measure》Carry out detection detection.
Measurement result see the table below：
| Testing index | Sample 1 | Sample 2 | Sample 3 | Palm oil (palm oil) |
| Sn-2 positions palmitic acid content/% | 74.5 | 66.2 | 67.5 | 11.0 |
| Total palmitic acid content/% | 45.2 | 40.0 | 40.2 | 45.0 |
| Sn-2 positions oleic acid content/% | 16.2 | 24.2 | 22.8 | 65.0 |
| Total oleic acid content/% | 41.1 | 45.8 | 45.8 | 40.0 |
| Sn-2 positions palmitic acid accounts for ratio/% of total palmitic acid | 54.9 | 56.0 | 56.0 | 8.1 |
| Sn-2 positions palmitic acid accounts for ratio/% of total fat | 24.8 | 22.5 | 22.5 | 3.7 |
| Sn-1+3 positions oleic acid accounts for ratio/% of total fat | 35.7 | 38.4 | 38.2 | 18.3 |
| OPO contents/% | 53.6 | 57.6 | 57.3 | 11.1 |
Calculate：
Sample 1：
Because 24.8/35.7 ＞ 0.5, the benchmark that is calculated according to the content of sn-1+3 positions oleic acid as OPO, i.e. OPO
Content is 35.7 2 × 3=53.6 of ÷.
Sample 1：
Because 22.5/38.4 ＞ 0.5, the benchmark that is calculated according to the content of sn-1+3 positions oleic acid as OPO, i.e. OPO
Content is 38.4 2 × 3=57.6 of ÷.
Sample 1：
Because 22.5/38.2 ＞ 0.5, the benchmark that is calculated according to the content of sn-1+3 positions oleic acid as OPO, i.e. OPO
Content is 38.2 2 × 3=57.3 of ÷.
Palm oil：
Because 3.7/11.0 ＜ 0.5, the benchmark that is calculated according to the content of sn-2 positions palmitic acid as OPO, i.e. OPO contains
Measure as 3.7 × 3=11.1.
Analysis：
It can be seen that palm oil is in two total palmitic acid content, total oleic acid content indexs, with InFatTMSample is sufficiently close to,
But according to the inventive method, the OPO content results that are calculated using OPO active parts as guiding relatively on, difference is huge.From
And advantage of the inventive method in terms of OPO measure is illustrated, avoid the adulterated possibility of active ingredient.
Claims (6)
1. a kind of method of indirect determination OPO content, described method is used to determine breast
OPO in product, methods described directly determine OPO (OPO) active part
(activeform), so that the method for OPO content further be calculated；So-called OPO active parts refer to postdigestive
OPO, that is, lose sn-1, the OPO of 3 oleic acid, and the method for the described content that OPO is further calculated is：
A) (if sn-2 position P)/(sn-1,3 position O) is less than or equal to 1:2, then it should be calculated on the basis of sn-2 positions P content
OPO content, i.e. the content of material of sn-2 positions P is exactly OPO content of material；
B) (if sn-2 position P)/(sn-1,3 position O) is more than 1:2, then it should calculate OPO with sn-1, on the basis of the O of 3 content
Content, i.e., 1/2 (sn-1,3 O) content of material is exactly OPO content of material.
2. according to the method for claim 1, it is characterised in that described dairy products include but is not limited to liquid milk, milk powder,
Formulated infant milk, Yoghourt, sour cream or ice cream.
3. method according to claim 1 or 2, it is characterised in that OPO digestion process includes following three parts：
1) fatty restriction endonuclease will be located at the aliphatic acid excision of triglycerides 1,3, form 2-monoglyceride；
2) undersaturated free oleic acid is solvable, and is efficiently absorbed；
3) 2-palmitic acid monoglyceride is efficiently absorbed.
4. according to the method for claim 3, it is characterised in that the side of sn-2 positions aliphatic acid composition in analysis dairy mixture
Method is GB/T24894-2010.
5. according to the method for claim 3, it is characterised in that the method for total fatty acids composition is in analysis dairy mixture
GB/T 22223‐2008。
6. according to the method for claim 3, it is characterised in that the sn-1, the measure of 3 oleic acid contents is by sn-2 positions oil
The measured value of sour and total oleic acid content is calculated.
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| CN106093270B (en) * | 2016-08-27 | 2017-09-15 | 江南大学 | A kind of sweet α fatty acid determination methods of three esters of animal and plant fat |
| CN107167547A (en) * | 2017-07-03 | 2017-09-15 | 圣元营养食品有限公司 | The content assaying method of the ester of 1,3 two oleic acid, 2 palmitic acid three in a kind of Milk Powder Formula For Infants |
| CN107621509A (en) * | 2017-09-27 | 2018-01-23 | 北京三元食品股份有限公司 | The method for quantitatively determining of the ester of 1,3 two oleic acid, 2 palmitic acid three in baby formula milk powder |
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| CN102175800A (en) * | 2011-01-07 | 2011-09-07 | 南京工业大学 | Method for measuring content of 1,3-dioleoyl-2-palmitoyl triglyceride in dairy products |
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| CN102175800A (en) * | 2011-01-07 | 2011-09-07 | 南京工业大学 | Method for measuring content of 1,3-dioleoyl-2-palmitoyl triglyceride in dairy products |
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| Title |
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| Candida sp.99-125脂肪酶催化猪油酸解合成1,3-二油酸-2-棕榈酸甘油三酯;李昕倩等;《生物加工过程》;20130531;第11卷(第3期);第14页1.3检测方法部分 * |
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